I was dreading taking a gym class in my senior year in high school. I missed gym in my junior year due to some surgery, so I had to take it as a senior in order to graduate. All of the other guys were juniors that i didn't know very well, but I had to make the best of it.
Partway into the school year, a new guy transferred to our school from Texas. Mark was eighteen like me, and a senior, and needed to take a gym class to graduate as well. We became friends and hung out together.
Being from so far away, Mark was pretty different than the rest of us Minnesotans. The accent and phrases were obvious, but in the locker room he was the only guy to wear A-shirts and boxer shorts. The rest of us wore standard tighty whitey briefs and t-shirts of various colors under our clothes. But Mark always wore white A-shirts and white boxers with some kind of little pattern.
One day while getting dressed, he was wearing a pair of white boxers with little red and blue shields on them. I finally commented, "Those are some cool boxers. No one else around here wears them."
"Thanks. At my old school, that's what every guy wore. I like how roomy they are. I don't think I could ever go back to briefs."
I think he liked the attention I was giving to his shorts, because I noticed a little tent forming as he pulled on his jeans.
I thought about his boxers a lot, and checked them out each day in the locker room. I wondered how they would feel. One day as Mark was dressing, he accidentally dropped a pair of boxers on the floor near my feet. I picked them up, and quickly inspected the green diamond pattern as I handed them to him. The material felt cool and crisp - I bet it would feel good against a cock and balls.
"You should get some boxers, man. I think you'd like them."
"My mom always buys us white briefs every Christmas. It would be weird to talk to her about buying me boxer shorts instead."
"You should come over some time. I'll let you borrow a pair of mine to see if you like them."
"Thanks, man. Maybe I'll do that."
I was both excited and a little scared to think about that. I was a little unsure about my sexuality, but that might be taking a big step to wear another guys underwear. Yet, those boxers where very intriguing...
I didn't bring it up the next day, but I could tell Mark was still thinking about it.
"Hey, Ray. You're pretty good in math. I'm having some problems in my class. Would you help me a little with my algebra assignment?"
"Sure. When do you have some time? Do you have a study hall?"
"No. But you could come over after school tonight. It's just me and my mom, and she works until six every night."
Was that an invitation? Or just a simple study request?
"Sure. I'll meet you by the front doors after school."
The rest of the day, I was thinking this might be a chance to try on a pair of boxer shorts. But I didn't know how to bring it up without sounding queer.
I met Mark by the door and we walked home to his house.
"I really appreciate the help, Ray. How can I repay you? Can trade you a pair of boxers for your time?"
"You don't have to pay me. I'm glad to help. Besides, if my mom found a new pair of underwear in our laundry, I would have some explaining to do."
"Well, you can at least try on a pair while you're over. You can decide if you like them, then ask your mom to buy you some for Christmas instead."
"Yeah, that's a good idea."
We got to Mark's house, which was empty like he said. I called my mom and told her where I was. He got out his algebra book on the kitchen table, then got us each a glass of soda. Then he went into his bedroom and came back with an A-shirt and pair of white boxers with little blue and red patterns.
"Here, Ray. You can try these on while we work and see if you like them. I brought you an A-shirt to try too."
"I don't want to sit here in just underwear in front of you."
"Why not? We are in underwear every day in the locker room. Here, I'll strip to my underwear now too.
Mark took off his shirt and pants. He had on his usual A-shirt and a pair of white boxers with thin blue stripes.
"Ok, I guess." I took the clothes he offered and asked, "Where is your bathroom to change?"
Mark laughed. "Ray, you change in front of me every day. It's not like I haven't seen you naked before."
I laughed too. "Sorry, you're right. I just didn't want to seem to weird to you."
I took off my shirt and pants, but modestly turned my back to Mark as I removed my briefs and t-shirt and pulled on his underwear. The crisp material felt great against my cock, which had plenty of room to start getting hard. I turned around and modeled them for Mark.
"They fit great. How do they look on me?"
"Wow, Ray. You look very cool. You should wear underwear like that all the time."
"I'll wear them for a while and see how I like them. Let's start on your homework."
I sat at the table, and Mark sat next to me. For the next half hour, we went over his assignment, and I tried to explain how to solve the problems. From time to time, I would catch Mark sneaking a look at my crotch, which only made me a little more excited. A few times, I had to adjust my cock in the shorts, so it wouldn't try to pop out the fly.
We finished the work, and still had about two hours until his mom came home.
"Well, how do you like the boxers and A-shirt?"
"I think I like them a lot. Now I'll have to figure out how to talk to my mom about getting me some for Christmas."
"What kind do you like? White, solid colors, patterns?"
I hadn't thought of that. I had just seen Mark's, which ran to white with patterns or stripes.
"Come on, I'll show you different kinds that I have."
